ORGN 295 |
Preparation, structure and chemistry of new pseudobenziodoxole-based hypervalent iodine reagents
| Viktor V. Zhdankin, Alexey Y. Koposov, and Dmitry N. Litvinov. Department of Chemistry, University of Minnesota Duluth, 10 University Drive, Duluth, MN 55812 |
| In the past decade, there has been a considerable interest and research activity centered on the chemistry of pentavalent iodine compounds. The well-known examples of these reagents are 2-iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP), which are widely used for the selective oxidation of primary and secondary alcohols and for a variety of other important oxidations. However both IBX and DMP have significant restrictions in their application in organic synthesis. Herein we will report the preparation, structure and reactivity of novel pentavalent iodine compounds, amides and esters of 2-iodylbenzoic and 2-iodylbenzenesulfonic acid (structures 1 and 2). These compounds were prepared by a dioxirane or bleach oxidation of the corresponding monovalent iodine starting materials and were isolated as non-explosive and soluble microcrystalline solids. These new representatives of the pseudocyclic hypervalent iodine compounds can selectively oxidize benzylic alcohols to aldehydes and organic sulfides to sulfoxides. 
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